The instant invention provides mixtures of C.sub.10 branched chain olefin epoxides which are used to augment or enhance the aroma of articles (e.g. clothing) subjected to the bleaching action of aqueous hypochlorite solutions subsequent to the drying of said articles after being subjected to such bleaching action. The instant invention also covers hypochlorite compositions which comprise aqueous hypochlorite, the said C.sub.10 branched chain olefin epoxides and one or more compounds having the generic structure: ##STR3## wherein at least one of R.sub.1 and R.sub.2 represents C.sub.10 -C.sub.12 branched or straight chain alkyl and when one of R.sub.1 or R.sub.2 is C.sub.10 -C.sub.12 branched or straight chain alkyl, the other of R.sub.1 or R.sub.2 is hydrogen; and wherein M.sub..alpha. and M.sub..beta. are the same or different and each represents sodium, potassium or lithium, said C.sub.10 -C.sub.12 moieties being either straight chain or branched chain, for example, having the structures: ##STR4## wherein the SO.sub.3.sup.- Na.sup.+ groups are at various positions on the phenyl moieties.
Chemical compounds which can provide woody, eucalyptol-like and minty aromas are desirable in the art of perfumery as well as in hypochlorite bleaches which include such perfuming materials. Many of the natural materials which provide such fragrances and contribute such desired nuances to perfumery compositions are high in cost, unobtainable at times, vary in quality from one batch to another, are unstable in aqueous hypochlorite bleaches, and/or are generally subject to the usual variations of natural products.
There is, accordingly, a continuing effort to find synthetic materials which will replace, enhance or augment the fragrance notes provided by certain natural essential oils or compositions thereof, particularly where perfumery materials which are stable in hypochlorite bleach compositions are desired. Unfortunately, many of the synthetic materials either have the desired nuances only to a relatively small degree, or they contribute undesirable or unwanted odor to the compositions and their stability, in most instances, is relatively low in the presence of aqueous hypochlorite bleaching solutions.
Aliphatic hydrocarbons are well known in the art of perfumery, e.g. myrcene, 2-methyl-6-methylene-2,7-octadiene, a constituent of lemon grass oil. Also found in lemon oil as well as in Bergamot oil, according to Gildemeister and Hoffmann, (Die Atherischen Ole, 3rd edition, Volume 1, page 301) is octylene, a long chain olefin containing eight carbon atoms.
Arctander, "Perfume and Flavor Chemicals, (Aroma Chemicals)", 1969, Vol. I, at monograph 974, discloses the use of "di-isoprene" in perfumery. Arctander states that di-isoprene is a mixture of 2,6-dimethyl-2,6-octadiene; 2,7-dimethyl-2,6-octadiene; and 3,6-dimethyl-2,6-octadiene. Arctander states that this material has a sweet, diffusive, somewhat "gassy" odor and, overall, is of very "little interest to the perfumer." At monograph 1074, Arctander discloses "dipentene" having a use in perfumery and indicates that this "dipentene" is 1-methyl-4-iso-propenyl-1-cyclohexene and indicates that it is useful in perfumery as a "lift" in citrusy fragrances and in the reconstruction of many essential oils such as Bergamot, Lime and Lemon.
U.S. Pat. No. 3,896,180 issued on July 22, 1975 discloses the use in perfumery of the cyclic diene epoxide having the structure: ##STR5## particularly for its woody, amber odor.
Other mono-epoxidized products of tri-methylcyclododecatriene are disclosed in U.S. Pat. No. 3,723,478 issued on Mar. 27, 1973. The uses in perfumery of such materials are also disclosed in said U.S. Pat. No. 3,723,478.
U.S. Pat. No. 3,333,010 issued on July 25, 1957 discloses epoxycyclododecadiene having the structure: ##STR6##
Nothing in the prior art discloses the use in conjunction with aqueous hypochlorite bleaching agents and with compounds having the generic structure: ##STR7## wherein one or both of R.sub.1 or R.sub.2 is branched or straight chain C.sub.10 -C.sub.12 alkyl and if one of R.sub.1 or R.sub.2 is C.sub.10 -C.sub.12 straight or branched chain alkyl, the other of R.sub.1 or R.sub.2 is hydrogen and wherein M.sub..alpha. and M.sub..beta. are the same or different and each is sodium, lithium or potassium, of diisoamylenes epoxides defined according to the generic structure: ##STR8## which would be produced from branched chain olefins having the generic structure: ##STR9## wherein R.sub.1 ', R.sub.2 ', R.sub.3 ', R.sub.4 ' and R.sub.5 ' are the same or different and each represents hydrogen or methyl with the proviso that (i) the sum total of carbon atoms in R.sub.1 ', R.sub.2 ', R.sub.3 ', R.sub.4 ' and R.sub.5 ' is three, and (ii) R.sub.1 ' and R.sub.2 ' represents hydrogen when R.sub.5 represents methyl, and (iii) when either R.sub.1 ' or R.sub.2 ' is methyl, R.sub.5 ' is hydrogen, the epoxide compounds being represented by the structures: ##STR10##
Furthermore, considerable difficulties have heretofore been encountered in using such compounded hypochlorite bleach or sterilizing solutions with perfumed oils so that a stable longlasting single phase commercially feasible bleach or sterilizing solution has been difficult to obtain, particularly wherein the desired aroma of the article bleached or sterilized (e.g. clothing) has a woody, eucalyptol-like and/or minty faint aroma on drying (and not the usual "hypochlorite-bleached-article" aroma). The problem has been defined in United Kingdom Patent Specification No. 886,084, published on Jan. 3, 1962 wherein it is stated that a stable "dispersion" of hypochlorite-resistant perfume in aqueous solutions of hypochlorites was formulated. United Kingdom Patent Specification No. 886,084 discloses the preparation of an aqueous "solution" of a hypochlorite containing a hypochlorite resistant perfume and a surface active quaternary ammonium compound of the betaine type soluble in the hypochlorite solution. Such ammonium compounds have the generic structure: ##STR11## wherein each of R.sub.1 ", R.sub.2 ", R.sub.3 " and R.sub.4 " are alkyl. One of the features of the perfumed solutions produced in accordance with said United Kingdom Patent Specification No. 886,084 is indicated to be that the solution exhibits foaming properties. Another feature of United Kingdom Patent Specification No. 886,084 is stated to be that the perfumed solutions covered by the patent are found to be clear and homogeneous after eight weeks of storage at room temperature. Nevertheless, betaines such as "Ambiteric D" as are discussed therein are not so broadly useful when used in concentrations of from 0.15% up to 4.0% (based on total weight of bleach or sterilizing solution) as to have the ability to be used in conjunction with woody, eucalyptol-like or minty types of perfume oils which should be incorporated into hypochlorite bleaches or sterilizers so that long lasting stable soluble single phase perfumed aqueous alkali metal hypochlorite bleach or sterilizing solutions having woody or eucalyptol-like or minty long lasting stable aromas are obtained, particularly where the quantity of perfume oil in the bleach or sterilizing substance is at levels of between 0.02% and 0.8% by weight of the total bleach or sterilizing solution. The need for the "woody", "eucalyptol-like" or "minty" aromas to be present in such bleach or sterilizing solutions exists so that the disagreeable characteristic "hypochlorite" aroma is substantially eliminated from aromas of the product to which the bleach or sterilizing solution is applied; particularly on dry-out, as well as from the aroma of the hands of the user when they are in direct contact with such bleach or sterilizing solutions.
U.S. Pat. No. 3,560,389 also discloses the feasibility of using perfume oils in hypochlorite bleaches or sterilizers at column 3, lines 37-40 but the disclosure is limited to inclusion of various detergents in addition to amine oxides, such as lithium lauryl sulfate and sodium lauryl ether sulfate and/or is further limited to include hydrotropes such as sodium xylene sulfonate in addition to the amine oxide. Exclusion of such hydrotropes and detergents additional to the amine oxides and diphenyl oxide derivatives of our invention is desirable not only to cause the perfume oils (which have the desired "eucalyptol-like" or "woody" or "minty" aromas) to function properly, but also from an ecological standpoint.
European Chemical News, Volume 13, Jan. 18, 1968, sets forth a synopsis of South African Pat. No. 67/4667 which corresponds to U.S. Pat. No. 3,560,389, but the reference also states at page 42:
"Alternatively, a detergent with bleaching or bacteriocidal properties can be formulated. Perfuming bleaching solutions is now possible." PA1 CLAIM: An aromatic liquid bleaching composition containing, as active ingredient, sodium hypochlorite, which comprises one or more of simple perfumes or compounded perfumes selected from the group consisting of anisole, benzophenone, benzylphenyl ether, bromelia, cedrenyl acetate, p-tertiary butylcyclohexanol, dimethylbenzylcarbinyl acetate, dihydroterpinyl acetate, diphenyl oxide, dimethylbenzylcarbinol, dimethylphenylcarbinol, dihydroterpineol, fenchyl acetate, fenchyl alcohol, p-methyldimethylbenzylcarbinol, methylphenylcarbinyl acetate, methyl-n-valerate, muskmoskene, muscarone, methylamyl ketone, phenylethyldimethylcarbinyl acetate, rose phenone, styrallyl propionate, tetra hydromuguol, tetra hydromuguyl acetate, tetrahydrolinalool, tetrahydrolinalyl acetate, verool, velveton, verdox, coniferan and yarayara, and a surface active agent which can stably be dissolved in an aqueous solution of sodium hypochlorite. PA1 Di-isoamylene is indicated to be synthesized in the following references: PA1 i--Murphy & Lane, Ind. Eng. Chem., Prod. Res. Dev., Vol. 14, No. 3, 1975 p. 167 (Title: Oligomerization of 2-Methyl-2-Butene is Sulfuric Acid and Sulfuric-Phosphoric Acid Mixtures). PA1 ii--Whitmore & Mosher, Vol. 68, J. Am. Chem. Soc. February, 1946, p. 281 (Title: The Depolymerization of 3,4,5,5-Tetramethyl-2-hexene and 3,5,5-Trimethyl-2-heptene in Relation to the Dimerization of Isoamylenes) PA1 iii--Whitmore & Stahly, Vo. 67, J. Am. Chem. Soc., December, 1945, p. 2158 (Title: The Polymerization of Olefins. VIII The Depolymerization of Olefins in Relation to Intramolecular Rearrangements. II) PA1 iv--U.S. Pat. No. 3,627,700, issued on Dec. 14, 1971, (Zuech) PA1 v--U.S. Pat. No. 3,538,181, issued on Nov. 3, 1970, (Banks) PA1 vi--U.S. Pat. No. 3,461,184, issued on August 12, 1969 (Hay, et al) PA1 vii--Gurwitsch, Chemische Berichte, 1912, Vol. 2, p. 796 (Production of Di-isoamylene From Isoamylene Using Mercury Acetate Catalyst)
Neither the South African nor the United States patents, however, indicate the advantages and usefulness of limiting the detergents either to (a) compounds having the generic structure: ##STR12## wherein at least one of R.sub.1 and R.sub.2 represents C.sub.10 -C.sub.12 straight chain or branched chain alkyl and when one of R.sub.1 or R.sub.2 is C.sub.10 -C.sub.12 branched or straight chain alkyl, the other or R.sub.1 or R.sub.2 is hydrogen and wherein M.sub..alpha. and M.sub..beta. are the same or different and each represents alkali metal which may be sodium, lithium or potassium, or (b) to mixtures of compounds having the structure: ##STR13## with at least one amine oxide defined according to the structure: ##STR14## of excluding from the formulation a hydrotrope or of specifying the nature of the perfume oil useful in the perfumed bleach or sterilizing solution (wherein A and B are each separately methyl or taken together, complete a morpholino ring and wherein R.sub.3 ''' is straight chain alkyl having from 11 up to 13 carbon atoms).
U.S. Pat. No. 3,876,551 in attempting to solve the foregoing problem discloses a stable single phase aqueous alkali metal hypochlorite liquid perfume bleach or sterilizing composition comprising an aqueous mixture of (1) an amine oxide composition consisting essentially of at least one morpholino and/or diethyl (C.sub.11 -C.sub.13 straight chain alkyl) amine oxide in an amount greater than 55% of said amine oxide composition, (2) at least one alkali metal hydroxide, (3) at least one alkali metal hypochlorite, and (4) a perfume oil compatible with the mixture capable of imparting a "woody" or a "floral" or a "clean fresh" or a "musk" or a "citrusy" note to the bleach or sterilizing composition; the mixture having a pH in the range of from 12 to 13.5 and the mixture excluding hydrotropes as well as all surfactants except the amine oxide. U.S. Pat. No. 3,876,551 also attempts to solve the foregoing problem by disclosing a process for producing the above-name mixture comprising the steps of combining an amide oxide composition consisting essentially of one or more morpholino and/or dimethyl C.sub.11 -C.sub.13 straight chain alkyl amine oxide(s) with the perfumed oil to form an amine oxide-perfume oil premix; admixing the amine oxide-perfume oil premix with an aqueous alkali metal hypochlorite solution, and combining an alkali metal hydroxide with the solution whereby the final pH of the mixture is from 12 up to 13.5. In a further effort to solve the foregoing problem U.S. Pat. No. 3,876,551 also discloses adjustment of the pH of the aqueous metal hypochlorite solution initially to the range of 12-13.5 and then combining the resulting pH-adjusted aqueous hypochlorite solution with the aforementioned premix. The resulting composition is indicated to cause products to which said composition is applied to have eliminated therefrom the disagreeable characteristic "hypochlorite" aroma and instead to have a "clean fresh" or "floral" or "woody" or "musk" or "citrusy" aroma to be imparted to the treated products. In addition, it is stated that the hands of the individual user after using and being in direct contact with the hypochlorite composition will not have the disagreeable characteristic "hypochlorite" aroma but instead will have a pleasant "clean fresh" or "floral" or "woody" or "musk" or "citrusy" aroma.
The disadvantage of the system of U.S. Pat. No. 3,876,551 however, concerns the relatively low degree of chemical stability and substantive stability of the perfume oil and of the single liquid phase system. Nothing in U.S. Pat. No. 3,876,551 indicates such a high degree of stabilities of the perfume-hypochlorite system as exists in the system of the present invention. Indeed, the stabilities using the system of the instant invention are far greater even at levels as low as 3% hypochlorite and are also relatively stable (from a standpoint of chemical stability of perfume oil, substantive stability of perfume oil and phase separation stability taken in combination with one another) at levels of as high as 10% hypochlorite in aqueous solution. Thus, the instant system gives rise to unexpected, unobvious and advantageous properties over the systems taught in the prior art.
Furthermore, nothing in the prior art including the teaching of U.S. Pat. No. 3,876,551 states either explicitly or implicitly the compatability of a thickener in the instant system, such as sodium palmitate, sodium stearate, potassium palmitate, potassium stearate, lithium palmitate, lithium stearate, lithium laurate, potassium laurate or sodium laurate whereby a stable gel (as opposed to a liquid) phase perfumed hypochlorite system or perfumed oil stabilizer emulsifier system "premix" may be produced.
The combination of the compound group having the structure: ##STR15## (wherein R.sub.1, R.sub.2, M.sub..alpha. and M.sub..beta. are defined, supra) with perfume and hypochlorite bleach in general, is set forth in the Kao Soap Company, Japanese Pat. No. 25514/79 filed on Nov. 2, 1973 and opened for public inspection on June 19, 1975. Thus, on page 2, at column 4, line 15, the compound: ##STR16## is disclosed for use in conjunction with the perfumed hypochlorite bleaches. The claim of the Kao Soap Patent is as follows:
Furthermore, the use of such compounds as those having the structure: ##STR17## (wherein R.sub.1, R.sub.2, M.sub..alpha. and M.sub..beta. have been previously defined) with hypochlorite bleaches is documented in the brochure of Dow Chemical entitled "DOWFAX Surfactants" and is covered in the Dow Chemical Company U.S. Pat. No. 3,172,861 issued on Mar. 9, 1965.
Nothing in the prior art discloses, however, the utility of the diisoamylene epoxide mixture or individual compounds of the instant application taken together with one of the compounds defined according to the generic structure: ##STR18## (wherein R.sub.1, R.sub.2, M.sub..alpha. and M.sub..beta. have been defined, supra) in hypochlorite bleaches, particularly where the hypochlorite concentration is greater than 7%. More particularly, nothing in the prior art discloses the use of such systems in conjunction with a thickener such as sodium palmitate, potassium palmitate, sodium stearate, potassium stearate, sodium laurate, potassium laurate lithium laurate, lithium stearate or lithium palmitate, whereby a stable gelled perfumed hypochlorite mixture is formed or whereby a "premix" gel-phase perfume oil-stabilizing/emulsifying agent is formed.
United Kingdom Pat. No. 796,130 published on June 4, 1958 discloses the synthesis of polyalkylindanes by means of, interalia, reacting alpha-methylstyrene with trimethylene (2-methylbutene-2) in the presence of an acid catalyst such as sulfuric acid or boron trifluoride diethyletherate. It is further indicated that such compounds are useful intermediates in the production of perfumery compounds. Apparently, however, the more volatile di-isoamylenes produced as side-products in the reaction of 2-methyl-butene-2 with alpha-methylstyrene are discarded.